The podcast dives into the controversial decision regarding Kyle Schwarber's non-tendering by the Chicago Cubs, highlighting the financial constraints that forced the team's hand during a tough financial period post-COVID. It reflects on how the Cubs may have misjudged player values, particularly in hindsight, considering Schwarber's consistent performance following his departure. The hosts question the rationale behind the decision, especially when the Cubs later signed Jock Peterson for slightly more money, suggesting a miscalculation in evaluating player worth.

Discussion extends to the trade of Yu Darvish, with the hosts pondering whether the Cubs truly capitalized on the potential returns from the trade, as many view Darvish's continued success as a blow to the Cubs' strategy. The episode scrutinizes the Cubs' management decisions, emphasizing a pattern of impatience and poor financial management that has led to regret over player selections and trade strategies.